US2329622A - Treatment of woolen textile materials - Google Patents

Treatment of woolen textile materials Download PDF

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Publication number
US2329622A
US2329622A US409036A US40903641A US2329622A US 2329622 A US2329622 A US 2329622A US 409036 A US409036 A US 409036A US 40903641 A US40903641 A US 40903641A US 2329622 A US2329622 A US 2329622A
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US
United States
Prior art keywords
melamine
wool
fabric
methylol
alkylated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US409036A
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English (en)
Inventor
Jr Edwin Parker Johnstone
Jr William Julius Van Loo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to LU28891D priority Critical patent/LU28891A1/xx
Priority to NL61889D priority patent/NL61889C/xx
Priority to US22566D priority patent/USRE22566E/en
Priority to BE467260D priority patent/BE467260A/xx
Priority to CA419781A priority patent/CA419781A/en
Priority to US409036A priority patent/US2329622A/en
Priority to US408991A priority patent/US2371892A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to GB11613/42A priority patent/GB562977A/en
Application granted granted Critical
Publication of US2329622A publication Critical patent/US2329622A/en
Priority to FR931376D priority patent/FR931376A/fr
Priority to ES0177535A priority patent/ES177535A1/es
Priority to DEA3364A priority patent/DE871885C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/368Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2369Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2385Improves shrink resistance
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2762Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]

Definitions

  • This invention relates to textiles and their treatment and more particularly to the treatment of wool and. wool containing fabrics to reduce their felting, fulling, and shrinking tendencies,
  • Wool and wool containing fabrics such as loose wool itself, yarns, threads, and woven, felted, and knitted cloth have a very undesirable tendency to felt and shrink when subjected to ordinary washing operations.
  • the tendency of these wool materials to felt and shrink is due gener ally to a curling and intertwining of the wool fibers as the fabrics are wetted and subjected to the mechanical movements of the washing process. As a result the fabric becomes more closely compacted, thicker, and has a considerably reduced area,
  • wool and wool containing fabrics such as unwoven wool, yarns, worsteds, tlannels, blankets, shirting, felts, knit goods, and others, whether of all wool or of part wool and part silk, synthetic silk, rayon, cotton, etc., may be rendered substantially resistant to felting, fulling, and shrinking by the application thereto of alkylated methylol-melamines such as will be presently described.
  • Our new shrink proofing process may be carried out in a safe, inexpensive, convenient and effective manner without any of the disadvantages of previously known processes.
  • the alkylated methylol-melamines which we employ in our shrink-proofing process are applied to the woolen goods in the form of solutions or dispersions containing from about 2 or 3 to 15% or more of the alkylated methylol-melamine.
  • the dispersions of alkylated methylol-melamines may be applied to the woolen fabrics in various ways known to those in the art.
  • the fabric to be treated is first thoroughly cleaned to remove fats and oils, etc.
  • the dry fabric is then immersed in the resin dispersion and passed through suitable rolls as in a padder or mangle to secure uniform impregnation and to remove excess resin,
  • the fabric may be impregnated by other methods such as for example by spraying or with suitable boxes located on the mangle.
  • suitable boxes located on the mangle As our invention is not limited to any particular method of impregnating the wool containing fabric, other methods will occur to those skilled in the art. Since shrink-proofing of woolen fabrics with alkylated methylolmelamine is most effective and economical within the range of about 5 to 15% by weight of resin based on the dried weight of fabric, the liquor pick-up should be governed accordingly.
  • the wool After the wool has been impregnated with the alkylated methylol-melamine dispersion, it is dried and the resin cured in situ by the application of elevated temperature.
  • a suitable catalyst may be added to the resin dispersion.
  • Such catalysts are known to chemists in the resin art. Oxalic acid, di-ammonium-hydrogen-phosphate and methyl acid pyrophosphate have been used by us with particuiar good results. Other catalysts such as triethanol amine phthalate, zinc chloride, acetic acid, dilute mineral acids, as HJC'l and others have been used with satisfactory results.
  • the curing temperatures may vary considerably from about 200 F. to about 300 F. with a corresponding reduction in time of cure with increase of temperature.
  • the curing operation is quite flexible, however, and may be varied to suit the equipment available to the process of where facilities do not allow the drying and curing temperatures to exceed 230 F.
  • the fabric after impregnation with the desired alkylated methylol-melamine may be framed to width, dried, batched up on the shell and allowed to stand hot to obtain a total drying and heating time of at least 45 minutes at 230 F. Where drying temperatures of 250 to 260 F. are available good results may be obtained by drying on the frame for 8 minutes at 250 to 260 F. and then passing the fabric through the drier a second time for 8 minutes at 260 F.
  • drying and curing procedure which has given good results is to dry the impregnating fabric on the frame for 8 minutes at 200 to 230 F. and then pass it through a frame or loop d'rler whereby the fabric will re- 2 asaaesa ceive heat treatment for 1 to 1% minutes at 300 F. Drying and curing times will also depend to some extent upon the eil'ectiveness of the particular curing accelerator employed and upon the nature of the fabric.
  • the wool fabric After the wool fabric has been treated as above described it should be given a short mild soaping before finishing which renders it soft and pliable. The fabric may then be given the usual finishing treatments such as decatizing, brushing, shearing, pressing, etc.
  • the alkylated methylol -melamlnes suitable for use in our process are preferably water dispersible or, as previously mentioned, may be dispersed with the aid of a solvent in order that they may be applied uniformly and economically to the fabric.
  • the various alkylated methylol-melamines may be prepared by diiferent processes, we prefer to prepare ours by first obtaining methylol-rnelamine, a productof the condensation of melamine with formaldehyde, and then reacting this product with a primary alcohol.
  • methylated methylolmelamine which is easily water dispersible and is the preferred alkylated methylol-melamine of our invention.
  • Various other allrylated melamine-formaldehyde condensation products may be prepared in a similar manner or by reacting the methylated methylol-melamine with other primary alcohols and obtaining by interchange the desired allwlatedproduct.
  • alkylating alcohols include ethyl alcohol, propyi alcohol, butyl alcohol, amyl alcohol, octyl alcohol, lauryl alcohol, ethylene glycol, diethyene glycol, propylene glycol and the glycol cthers known to the trade as "Carbitols such for example being the monobutyl ether of (ii-ethylene glycol,
  • the alkylated melamine-formaldehyde condensation products employed by us in the treatment of wool and wool containing fabrics to prevent their felting, fulling and shrinking are prepared by known methods.
  • the melamineformaldehyde condensation product which we prefer to alkylate is prepared by reacting 2 to 6 molds of formaldehyde with 1 mol of melamine.
  • the condensation product formed is believed to be mostly methylol-melamine. Although it is theoretically possible to react 6 mols of formaldehyde with 1 moi of melamine, this degree of reaction is not always attained due to excessive polymerization of the reaction mixture.
  • butyl carbitolated methylmelamine 600 parts by weight of the above described 50% solution of methylated methylolmelamine and 160 parts by weight of butyl carbitol were mixed and heated to concentrate the mixture to 408 parts by weight, whereupon, a composition consisting of about 75% of the butyl car-belated methylol-melamine was obtained.
  • Ethylated methylol-melamine, butylated methylol-melamine, and the other alkylated methylol-melamines previously described may also be prepared in a similar way.
  • the impregnated woolen swatches were then cured for minutes at 260* F. and then washed, with a control sample 9" by 23" of the same fabric, in a standard washing machine using a temperature oi 120 F. and a soap concentration. After periods of 15 minutes, 30 minutes. and one hour the swatches were rinsed with warm water, squeezed, and dried flat without tension. The percent of shrinkage after each washing period is shown in the following table:
  • a process of reducing the felting and shrinking tendencies of wool containing fabrics which comprises impregnating a wool containing fabric with an aqueous dispersion of a water dispersible, substantially unpolymerized alkylated melamine-formaldehyde condensation product the take-up of the aqueous dispersion being such as to deposit in the fabric from 2%% to 15% 4 aszaeaa by weight based on the dry weight of the fabric of the water dispersible alkylated melamineformaidehyde condensation product and thereafter subjecting the impregnated fabric to an elevated temperature sufficient to cure the alkyiated melamine-formaldehyde condensation product therein to a substantially water-insoluble condition.
  • a process of reducing the felting and shrinking tendencies of wool containing fabrics which comprises impregnating a wool containing fabric with an aqueous solution of a water soluble, substantially unpolymerized methylated metnylol melamine condensation product the take-up of the aqueous solution being such as to deposit in the fabric from il to 15% by weight based on the dry weight of the fabric of the water soluble methylated methylol melamine condensation product and thereafter subjecting the im pregnated fabric to an elevated temperature suflicient to cure the methylated methyioi melamine condensation product th'erein to a substantially water-insoluble condition.
  • a process of reducing the felting and shrinking tendencies of wool containing fabrics which comprises impregnating wool containing fabrics with an aqueous dispersion of a water dispersibie substantially unpolymerized ethylated methyloi melamine condensation product the take-up of the aqueous dispersion being such as to deposit in the fabric from 2 2% to 15% by weight based on the dry weight of the fabric of the water dispersible ethylated methylol melamine condensation product and thereafter subjecting the impregnated fabric to an elevated temperature suflicient to cure the ethylated methylol melamine condensation product therein to a substantially water-insoluble condition.
  • a process of reducing the felting and shrinking tendencies of wool containing fabrics which comprises impregnating a wool containing fabric with an aqueous dispersion of a water dispersible substantially unpolymerized condensation product of the monobutyi ether of diethylene glycol with methylol melamine the take-up of the aqueous dispersion being such as to deposit on the wool containing fabric from 2 /2% to 15% by weight based on the dry weight of the wool of the said condensation product and thereafter subjecting the impregnated fabric to an elevated temperature sufficient to cure the said condensation product contained in the fabric to a substantially water-insoluble condition.
  • a process of reducing the felting and shrinkt dencies oi woolen fabrics which comprises iigpregnating a wool fabric with an aqueous dis- 9 rsion of a water dispersible substantially unpolymerized alkylated melamine-formaldehyde condensation product the take-up of the aqueous dispersion being such as to deposit on the wool fabric from 2 to 15% by weight based on the dry weight of the wool fabric of the alkylated melamine-formaldehyde condensation product and thereafter subjecting the impregnated wool fabric to a temperature within the range of 200 F. to 300 F., to cure the alkylated melamineformaldehyde condensation product therein to a substantially water-insoluble condition.
  • a wool containing fabric resistant to felting and shrinking containing 2/z% to 15% by weight of a heat cured, substantially water insoluble, alkylated melamine-formaldehyde condensation product said wool containing fabric having been impregnated with an aqueous dispersion of a water dispersible substantially unpolymerlzed alkylated melamine-formaldehyde condensation product in accordance with the method of claim 1.
  • a wool containing fabric resistant to felting and shrinking containing il to 15% by weight of a heat cured, substantially water-insoluble methylated methylol melamine polymer, said wool containing fabric having been impregnated with an aqueous solution of a watersoluble, substantially unpolymerized methylated methyiol melamine in accordance with the method of claim 2.
  • a process of reducing the felting and shrinking tendencies of wool which comprises cleaning wool to remove all fats and oils therefrom and impregnating the clean wool with an aqueous dispersion of a substantially unpolymerized.
  • aikylated methylol-melamine condensation product the take-up of the dispersion being such as to deposit on the wool from 2'/ to 15% by weight based on the dry weight of the wool of the alkylated methylol-melamine condensation product and thereafter drying and heating the impregnated wool at a temperature within the range of 200 C. to 300 C. to polymerize the alkyiated methylol-melamine condensation product on the wool to a substantially water-insoluble condition.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US409036A 1941-08-30 1941-08-30 Treatment of woolen textile materials Expired - Lifetime US2329622A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US22566D USRE22566E (en) 1941-08-30 Treatment of woolen textile
BE467260D BE467260A (en(2012)) 1941-08-30
CA419781A CA419781A (en) 1941-08-30 Wool and fabric treating process
LU28891D LU28891A1 (en(2012)) 1941-08-30
NL61889D NL61889C (en(2012)) 1941-08-30
US408991A US2371892A (en) 1941-08-30 1941-08-30 Permanent finish for textiles
US409036A US2329622A (en) 1941-08-30 1941-08-30 Treatment of woolen textile materials
GB11613/42A GB562977A (en) 1941-08-30 1942-08-18 Improvements in or relating to methods of reducing the tendency of wool and wool-containing fabrics to felt and shrink
FR931376D FR931376A (fr) 1941-08-30 1946-07-25 Perfectionnements au traitement de la laine et des tissus contenant de la laine
ES0177535A ES177535A1 (es) 1941-08-30 1947-04-11 Un procedimiento de reducir la tendencia al afieltrado y al encogimiento de la lana
DEA3364A DE871885C (de) 1941-08-30 1950-09-03 Verfahren zur Verminderung der Verfilz- und Schrumpfneigung von Wolle

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US409036A US2329622A (en) 1941-08-30 1941-08-30 Treatment of woolen textile materials

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US2329622A true US2329622A (en) 1943-09-14

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US22566D Expired USRE22566E (en) 1941-08-30 Treatment of woolen textile
US409036A Expired - Lifetime US2329622A (en) 1941-08-30 1941-08-30 Treatment of woolen textile materials

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Application Number Title Priority Date Filing Date
US22566D Expired USRE22566E (en) 1941-08-30 Treatment of woolen textile

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US (2) US2329622A (en(2012))
BE (1) BE467260A (en(2012))
CA (1) CA419781A (en(2012))
DE (1) DE871885C (en(2012))
ES (1) ES177535A1 (en(2012))
FR (1) FR931376A (en(2012))
GB (1) GB562977A (en(2012))
LU (1) LU28891A1 (en(2012))
NL (1) NL61889C (en(2012))

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416884A (en) * 1942-09-09 1947-03-04 Du Pont Methylated methylolmelamine as a fixing agent for dyed cotton textiles
US2453308A (en) * 1943-07-21 1948-11-09 Monsanto Chemicals Polyvinyl butyral composition
US2484962A (en) * 1945-09-07 1949-10-18 Montclair Res Corp Diolefin-nitrile copolymer bath for shrinkproofing wool
US2491454A (en) * 1944-10-04 1949-12-13 American Cyanamid Co Nonslip fabrics and method of preparation thereof
US2491584A (en) * 1945-09-07 1949-12-20 Montclair Res Corp Shrinkproofing wool and materials therefor
US2499653A (en) * 1946-10-17 1950-03-07 American Cyanamid Co Treatment of protein-containing textile materials and products thereof
US2501435A (en) * 1947-06-11 1950-03-21 American Cyanamid Co Treatment of woolen pile fabrics
US2503629A (en) * 1948-06-23 1950-04-11 Orr Felt And Blanket Company Web carrier and method of making same
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
US2522338A (en) * 1945-02-19 1950-09-12 Eavenson & Levering Company Process for shrink-proofing wool and woolen fabrics
US2526637A (en) * 1948-04-02 1950-10-24 Du Pont Shrinkproofed wool and method of producing same
US2537131A (en) * 1947-07-18 1951-01-09 American Cyanamid Co Continuous process for the preparation of alkylated alkylol melamine
US2539365A (en) * 1948-08-12 1951-01-23 American Cyanamid Co Treatment of wool-containing textile materials
US2539366A (en) * 1948-08-12 1951-01-23 American Cyanamid Co Treatment of wool-containing textile materials
US2581296A (en) * 1947-08-04 1952-01-01 Hat Corp America Treated fur fibers
US2609307A (en) * 1949-11-14 1952-09-02 American Cyanamid Co Treatment of wool with acid aminotriazine resin colloids
US2622996A (en) * 1947-11-28 1952-12-23 Monsanto Chemicals Treatment of heavy materials comprising keratinous fibers
US2632717A (en) * 1947-02-07 1953-03-24 Ciba Ltd Process for improving the resistance of wool to felting and shrinking
US2663616A (en) * 1949-04-27 1953-12-22 Ciba Ltd Method for treating wool
US2723213A (en) * 1951-07-28 1955-11-08 Monsanto Chemicals Treatment of yarns comprising keratinous fibers
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US2807557A (en) * 1951-04-16 1957-09-24 Clifford R Carney Method of treating furs
US2897041A (en) * 1955-07-18 1959-07-28 Geigy Ag J R Process to reduce the felting and creasing of wool
US3017292A (en) * 1954-06-18 1962-01-16 Hugh H Mosher Fire retardant nylon fabric and method of producing the same

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE463771A (en(2012)) * 1945-03-09 1900-01-01
US2484599A (en) * 1945-06-06 1949-10-11 Alrose Chemical Company Process of reducing the shrinkage and felting tendencies of protein textile materials
GB615473A (en(2012)) * 1945-08-13
US2545450A (en) * 1948-02-18 1951-03-20 Pacific Mills Resin treatment of wool fabric
US2515107A (en) * 1948-03-04 1950-07-11 American Cyanamid Co Method of treating wool-containing textile materials
US2514132A (en) * 1948-03-05 1950-07-04 American Cyanamid Co Textile-finishing composition, method of treating wool-containing textile material therewith and product thereof
US2702258A (en) * 1950-03-07 1955-02-15 American Cyanamid Co Hydrous oxide containing resinous compositions
US2709693A (en) * 1950-12-04 1955-05-31 Ciba Ltd Etherified condensation products of formaldehyde with amino-1:3:5-triazines containing at least two aminogroups
US3212955A (en) * 1962-05-10 1965-10-19 American Cyanamid Co Tire cord bonding with polymethylolmelamine resins
EP0080272A3 (en) * 1981-10-28 1984-08-22 South African Inventions Development Corporation Shrink-resist treatment of wool
CN102505302A (zh) * 2011-10-18 2012-06-20 常州市武进丰盛针织有限公司 针织呢绒面料的生产工艺

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT150002B (de) * 1935-09-28 1937-06-25 Chem Ind Basel Verfahren zur Herstellung von Aldehyd-Kondensationsprodukten.

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416884A (en) * 1942-09-09 1947-03-04 Du Pont Methylated methylolmelamine as a fixing agent for dyed cotton textiles
US2453308A (en) * 1943-07-21 1948-11-09 Monsanto Chemicals Polyvinyl butyral composition
US2491454A (en) * 1944-10-04 1949-12-13 American Cyanamid Co Nonslip fabrics and method of preparation thereof
US2522338A (en) * 1945-02-19 1950-09-12 Eavenson & Levering Company Process for shrink-proofing wool and woolen fabrics
US2491584A (en) * 1945-09-07 1949-12-20 Montclair Res Corp Shrinkproofing wool and materials therefor
US2484962A (en) * 1945-09-07 1949-10-18 Montclair Res Corp Diolefin-nitrile copolymer bath for shrinkproofing wool
US2499653A (en) * 1946-10-17 1950-03-07 American Cyanamid Co Treatment of protein-containing textile materials and products thereof
US2632717A (en) * 1947-02-07 1953-03-24 Ciba Ltd Process for improving the resistance of wool to felting and shrinking
US2509174A (en) * 1947-05-22 1950-05-23 Monsanto Chemicals Process of waterproofing textile fabrics
US2501435A (en) * 1947-06-11 1950-03-21 American Cyanamid Co Treatment of woolen pile fabrics
US2537131A (en) * 1947-07-18 1951-01-09 American Cyanamid Co Continuous process for the preparation of alkylated alkylol melamine
US2581296A (en) * 1947-08-04 1952-01-01 Hat Corp America Treated fur fibers
US2622996A (en) * 1947-11-28 1952-12-23 Monsanto Chemicals Treatment of heavy materials comprising keratinous fibers
US2526637A (en) * 1948-04-02 1950-10-24 Du Pont Shrinkproofed wool and method of producing same
US2503629A (en) * 1948-06-23 1950-04-11 Orr Felt And Blanket Company Web carrier and method of making same
US2539365A (en) * 1948-08-12 1951-01-23 American Cyanamid Co Treatment of wool-containing textile materials
US2539366A (en) * 1948-08-12 1951-01-23 American Cyanamid Co Treatment of wool-containing textile materials
US2663616A (en) * 1949-04-27 1953-12-22 Ciba Ltd Method for treating wool
US2609307A (en) * 1949-11-14 1952-09-02 American Cyanamid Co Treatment of wool with acid aminotriazine resin colloids
US2807557A (en) * 1951-04-16 1957-09-24 Clifford R Carney Method of treating furs
US2723213A (en) * 1951-07-28 1955-11-08 Monsanto Chemicals Treatment of yarns comprising keratinous fibers
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US3017292A (en) * 1954-06-18 1962-01-16 Hugh H Mosher Fire retardant nylon fabric and method of producing the same
US2897041A (en) * 1955-07-18 1959-07-28 Geigy Ag J R Process to reduce the felting and creasing of wool

Also Published As

Publication number Publication date
NL61889C (en(2012)) 1900-01-01
GB562977A (en) 1944-07-25
USRE22566E (en) 1944-11-21
BE467260A (en(2012)) 1900-01-01
ES177535A1 (es) 1947-06-01
DE871885C (de) 1953-03-26
FR931376A (fr) 1948-02-20
CA419781A (en) 1944-04-25
LU28891A1 (en(2012))

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